MetaCyc Pathway: dimethylsulfoniopropanoate biosynthesis III (algae)

Enzyme View:

Pathway diagram: dimethylsulfoniopropanoate biosynthesis III (algae)

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: DMSP biosynthesis, dimethylsulfoniopropionate biosynthesis III (algae)

Superclasses: Biosynthesis Other Biosynthesis Organic Solutes Biosynthesis Dimethylsulfoniopropanoate Biosynthesis

Some taxa known to possess this pathway include ? : Emiliania huxleyi , Melosira nummuloides , Tetraselmis , Ulva intestinalis , Ulva lactuca

Expected Taxonomic Range: Chlorophyta , Haptophyceae , Rhodophyta , Stramenopiles

General Background

Dimethylsulfoniopropionate (DMSP) is an osmolyte of many marine algae and certain plants [Otte04]. In marine phytoplankton DMSP is also used as a predator deterrent and an antioxidant [Howard06].

Biological degradation of DMSP is the main source for dimethyl sulfide (DMS) in the marine environment [Yoch02] (see dimethylsulfoniopropanoate degradation I (cleavage)). The degradation of DMSP to DMS and subsequent exchange of DMS across the ocean-atmosphere boundary is the main natural source of sulfur to the atmosphere. The flux of DMS from the ocean to the atmosphere is estimated at about 1.5 x 10(13) g of sulfur annually. Once in the atmosphere, DMS plays a major part in cloud formation and potentially in climate regulation.

About This Pathway

Initial studies performed with the green macroalga Ulva lactuca showed that L-methionine was the source of the sulfur atom and both methyl groups in DMSP, and that the α carbon of methionine was the source of the carboxyl group [Greene62, Kahn64]. However, the exact sequence of reactions was not determined until much later, when the pathway for DMSP biosynthesis in the related alga Ulva intestinalis was confirmed by in vivo isotope labelling [Gage97].

Starting from methionine, the pathway includes transamination, reduction, and S-methylation (in this order) producing the novel sulfonium compound dimethylsulfonio-2-hydroxybutanoate, which is oxidatively decarboxylated to DMSP.

The pathway intermediates were found in several other species, including the prymnesiophyte Emiliania huxleyi, the diatom Melosira nummuloides, and a species of Tetraselmis, a prasinophyte [Gage97].

As of 2008, none of the enzymes that participate in this pathway has been characterized.

Variants: dimethylsulfoniopropanoate biosynthesis I (Wollastonia) , dimethylsulfoniopropanoate biosynthesis II (Spartina)

Created 24-Sep-2008 by Caspi R , SRI International


Gage97: Gage DA, Rhodes D, Nolte KD, Hicks WA, Leustek T, Cooper AJ, Hanson AD (1997). "A new route for synthesis of dimethylsulphoniopropionate in marine algae." Nature 387(6636);891-4. PMID: 9202120

Greene62: Greene, R. C. (1962). "Biosynthesis of dimethyl-{beta}-propiothetin." J. Biol. Chem. 237: 2251 - 2254.

Howard06: Howard EC, Henriksen JR, Buchan A, Reisch CR, Burgmann H, Welsh R, Ye W, Gonzalez JM, Mace K, Joye SB, Kiene RP, Whitman WB, Moran MA (2006). "Bacterial taxa that limit sulfur flux from the ocean." Science 314(5799);649-52. PMID: 17068264

Kahn64: Kahn, V. (1964). "Glycine as a Methyl Donor in Dimethyl-(beta)-Propiothetin Synthesis." Journal of Experimental Botany 15 (2) : 225-231.

Otte04: Otte ML, Wilson G, Morris JT, Moran BM (2004). "Dimethylsulphoniopropionate (DMSP) and related compounds in higher plants." J Exp Bot 55(404);1919-25. PMID: 15181109

Yoch02: Yoch DC (2002). "Dimethylsulfoniopropionate: its sources, role in the marine food web, and biological degradation to dimethylsulfide." Appl Environ Microbiol 68(12);5804-15. PMID: 12450799

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Berger03: Berger BJ, English S, Chan G, Knodel MH (2003). "Methionine regeneration and aminotransferases in Bacillus subtilis, Bacillus cereus, and Bacillus anthracis." J Bacteriol 185(8);2418-31. PMID: 12670965

Dolzan04: Dolzan M, Johansson K, Roig-Zamboni V, Campanacci V, Tegoni M, Schneider G, Cambillau C (2004). "Crystal structure and reactivity of YbdL from Escherichia coli identify a methionine aminotransferase function." FEBS Lett 571(1-3);141-6. PMID: 15280032

Heilbronn99: Heilbronn J, Wilson J, Berger BJ (1999). "Tyrosine aminotransferase catalyzes the final step of methionine recycling in Klebsiella pneumoniae." J Bacteriol 1999;181(6);1739-47. PMID: 10074065

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Schuster06: Schuster J, Knill T, Reichelt M, Gershenzon J, Binder S (2006). "Branched-chain aminotransferase4 is part of the chain elongation pathway in the biosynthesis of methionine-derived glucosinolates in Arabidopsis." Plant Cell 18(10);2664-79. PMID: 17056707

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Tue Mar 31, 2015, biocyc12.